Isovanillin → HCID 59333888, compound

HRID 1616777Notes

Reaction equation

[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C[C:13]1[CH:18]=[CH:17][C:16](S(OCCC#CCC)(=O)=O)=[CH:15][CH:14]=1>>[CH2:17]([O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:2]=[O:1])[CH2:18][C:13]#[C:14][CH2:15][CH3:16]

Participants

Reactant 2

HCID 12127Isovanillin

HCID 14967550HCID 14967550, compound

Product 1

HCID 59333888HCID 59333888, compoundYield 50%

Procedure

Isovanillin (0.76 g, 5.0 mmol) was alkylated with hex-3-ynyl 4-methylbenzenesulfonate (1.9 g, 7.53 mmol) according to Procedure 4. The crude product was recrystallised from EtOAc/petrol to provide 3-(hex-3-ynyloxy)-4-methoxybenzaldehyde (0.58 g, 50%) as a colourless crystalline solid; mp 86.5-87.5° C.; δH (400 MHz, CDCl3) 1.13 (t, J=7.6 Hz, 3H, CH3), 2.17 (tq, J=7.6, 2.4 Hz, 2H, CH3CH2), 2.72 (tt, J=7.6, 2.4 Hz, 2H, OCH2CH2C), 3.95 (s, 3H, OCH3), 4.17 (t, J=7.6 Hz, 2H, OCH2), 6.98 (d, J5,6=8.0 Hz, 1H, H5), 7.44 (d, J2,6=1.6 Hz, 1H, H2), 7.47 (dd, J5,6=8.0, J2,6=1.6 Hz, 1H, H6), 9.85 (s, 1H, CHO); δC (100 MHz, CDCl3) 12.4, 14.1, 19.6, 56.2, 67.6, 74.5, 83.9, 110.8, 111.0, 126.9, 130.1, 148.6, 154.8, 190.8; vmax 1019, 1134, 1265, 1586, 1683, 2841, 2977 cm−1.

Workup

customThe crude product was recrystallised from EtOAc/petrol

Sources & evidence

ORD record: ord-625cf43d3d99451abb5ffa43bdf269bd
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765812B2

Reaction notes

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